nee~ i also thought that kind of idea.. if only possible i would like to tell the author that undertaker is Ciel's true mother!! hahah MPreg sorry heheh .. but true to my words i also thought about that. ε=ε=(ノ≧∇≦)ノ
What everyone fails to remember here is that Undertaker was a Shinigami for a long time before he fled the job to become the Undertaker - he was considered the best at what he did, and that as the Undertaker he was a contact for Vincent - so he could not have been Vincent's friend prior to becoming a Shinigami. King (below) also thinks that Undertaker was close to the family prior to his 'suicide" but that still does not fit the timeline.
hey hey everyone i just got a crazy idea
what if undertaker is the blond boy next to the earl in the pic and he loved the earl and after his death he commited suicide what do you say???